Every Job Search Mistake I've Seen Starts In The Same Place

JOB SEARCH STRATEGY WITH EARLY.

I was looking at LinkedIn yesterday and realized I just passed four years of helping startup job seekers land roles.

It’s kind of crazy that I’m approaching the halfway point of my time spent at Uber.

As I reflected on the last four years, something came up that I wanted to focus on this week.

At this point, I've seen hundreds of job searches up close.

Early members, people in my network, family, friends, and candidates I interviewed across seven years at Uber and two years in a Series A/B startup.

From seeing that many job searches, patterns begin to emerge.

The job searches I’ve seen drag on the longest, produce the most frustration, and yield the fewest offers almost always have one thing in common.

They started taking action without knowing where they were going.

Which means every application they sent, every message they wrote, every interview they prepped for, was built on a non-existent foundation.

This is the step most people skip, and yet it is the single thing that speeds up a job search more dramatically than any outreach technique or interviewing strategy ever could.

A THEORY ABOUT WHY JOB SEARCHES TAKE 6 MONTHS

Per the Bureau of Labor Statistics, the average duration of unemployment in the US has hovered between 5 and 7 months for almost a decade.

Here’s my theory for why those numbers don’t move much, even when the market does.

Most job seekers spend their first three days updating their LinkedIn profile and resume. 

They then spend the following three months in trial and error, unsure of what they want and where they’re going, and often resort to applying to the most familiar companies (even though they don’t want to work at those companies) to reduce the risk of rejection.

During those three months, they collect a lot of rejections and ghosting, and it ultimately leads in two directions:

1. Spray and Pray: It pushes them to get desperate and apply to anything and everything just to land something. Anything to make the rejection stop.

2. Targeted Approach: They begin identifying which conversations are easiest and why. They get a feel for what job descriptions make them want to do whatever it takes to land the role, while others make them want to run far, far away. They get enough signal to figure out what they actually want.

For the poor spray-and-pray, they become the long tail of job-search data. These are the folks who end up with 8-month, 10-month, and 12+ month job searches.

For those who adopt the targeted approach, it takes another 3 months of focused work to pursue the role they want before they land it.

3 months to get clear + 3 months of targeting that role = 6 months on the search.

But does that clarity process need to be done in 3 months?

What if it could be done in one week?

That would cut the job search process from 6 months to 3 months.

Well… the clarity work can be done in a week.

It doesn’t need to be perfect (it’ll be directionally positive and can be adjusted going forward).

It’s not the most comfortable work (that’s why most people avoid doing it).

But the deliberate, thoughtful work you put in up front before you ever touch your resume or send an application can collapse the first three months down to several days and cut your total job search period in half or more.

Clarity first job searches are shorter searches that lead to a higher probability of enjoying your new role. 

And how to execute a clarity first job search is exactly what we’ll cover in today’s newsletter.

Table of Contents

• Why starting without clarity costs you more time than building it would have

• The Past audit: what your history is actually telling you

• The Present audit: the no-BS assessment most people avoid

• The Future: building a picture vivid enough to run toward

• How to combine all three into your Ideal Job Description

• Download the free playbook

STEP 1: AUDITING YOUR PAST

To start off your job search, I recommend following my Complete Career Clarity framework.

The first part of the CCC framework is a deep look at every role you’ve ever worked in.

This is not a summary of your resume.

What you need is an analysis of:

• What lit you up

• What drained you

• When were you at your best, and what the environment looked like

• When were you at your worst, and what the environment looked like

• What is the highlight reel of accomplishments

Most people skip this and find themselves back in an environment and role that led them to look for their next job in the first place.

As counterintuitive as it sounds, if you want to move forward, you first need to look backward.

Your past is the most reliable data set you have.

It will tell you which environments you thrive in. Which types of problems you’re actually good at and enjoy solving. Which roles looked good on paper but cost you something you didn’t notice until later.

They’ll show you the green lights to run toward and the red flags to identify and run away from when they arise.

It’ll help you craft better questions in networking conversations and interviews to uncover whether the company and role are the right fit for you.

First, write everything down. Then, analyze your past. I guarantee you that common themes will arise. 

You can use those themes as you hone in on the ideal next step for you and your career.

I’ve put all of the steps and prompts (which you can copy and paste) into this playbook.

STEP 2: AUDITING YOUR PRESENT

The second part of the process is to run a no-BS assessment on where you actually are today.

This is not where you want to be.

It’s not the version of yourself you’d describe in an interview.

I’m talking about the real skills, real experiences, real network, and honest read on the gaps between where you are today and where you want to go.

Without this exercise, there are two potential paths.

• You will either overestimate what you have, which produces applications for roles you’re not ready for or roles that would not be a good fit.

• You underestimate what you have, which produces applications for roles that won’t challenge you or will result in you “self-rejecting” roles that would be perfect for you before you even apply.

A good no-BS self-assessment asks three questions:

1. What can I do exceptionally well right now? What am I world-class at?

2. What am I not great at? What do I struggle with?

3. Do I want to get better at the things I struggle with or avoid roles where that’s a main component?

I recommend asking yourself these questions and then recruiting a squad of coworkers, managers, and cross-functional peers to give you feedback on the same.

Steal this script when asking them for feedback:

"Hey [FIRSTNAME], I’m going through an exercise to understand my strengths and weaknesses and would love some feedback. When we were working together, what would you say were the top things that I was great/good at, and what things would you say were my biggest weaknesses? I’m trying to grow and identify blind spots, so don’t worry about hurting my feelings. I’m trying to create a no-BS self-assessment."

As with the past audit, you’ll find themes present across your personal introspection and the feedback you receive.

This exercise isn’t designed to make you feel bad about yourself. It’s to uncover hidden strengths you didn’t know existed and areas where you’re less proficient, so you can avoid or improve them.

Knowing yourself provides an accurate starting point and will inform your strategy better than an assumed or imagined sense of capability.

IMPORTANT NOTE: One thing I’ve seen personally from running this exercise is how it reveals the superpowers that you didn’t know existed. Your superpowers are likely invisible to you. The reason they’re invisible is that you’re likely so good at them and they come so easily to you that you believe everyone can do them.

In reality, your level of proficiency is uncommon. These are the exact skills, traits, and abilities to leverage in the job search going forward.

STEP 3: BUILDING A PICTURE VIVID ENOUGH TO RUN TOWARD

As you can see, you’ve run through a few exercises to understand yourself before identifying where it is you want to go.

The third part of the process is building a compelling picture of your future.

The goal is to paint a picture so vivid you can feel it, smell it, taste it.

This is the specific vision of what you want your working life to look like in two to five years.

The type of company you want to be in.

The problems you want to be solving.

The people you want to be working with.

The version of yourself you want to become.

Most people set career goals the way they set New Year’s resolutions.

Vague. Unanchored. Abandoned in a few weeks.

The future audit works differently because it’s designed to produce one specific output: your Ideal Job Description

When you develop this picture, close your eyes. Feel what it feels like to be in that role. What does it feel like? Where do you feel it in your body?

Then do the opposite. Imagine sitting in one of your prior roles where you dreaded coming into work every day. Close your eyes and feel what that feels like. Where do you feel that feeling in your body?

You can use these feelings in your job search.

As you read a job description, which of those feelings do you feel? The ideal future state or the dreaded past state? That’s a good indication of whether it’s worth your time.

Your goal here is not to predict the future.

You’re building a target clear enough that you’ll recognize the right role when it appears and pass on the wrong ones without second-guessing yourself.

DON’T JOB SEARCH ALONE

If you’re reading through this thinking “I want help to do this step-by-step” that’s exactly what the Early Accelerator is built for.

Here’s what our members get:

One Early member recently landed a remote senior leadership role at a $500M startup that wasn’t even hiring.

Another went from VP to a COO role less than 90 days after joining.

These aren’t flukes - they’re the result of the playbooks, mentorship, company research, and community we provide.

It’s the best way I’ve found to cut through the noise and land a role at the next generation of world-changing startups.

Learn more and apply today (click here).

FINAL STEP: YOUR IDEAL JOB DESCRIPTION

Now that we have your past, present, and future, it’s time to combine them into a coherent target for you to go after.

This is what I call your Ideal Job Description.

Your Ideal Job Description is a list of characteristics your next role needs to have for you to enjoy the work, grow toward your compelling future, and build something worth having, regardless of the company’s outcome.

This becomes the filter for every decision you make in your job search.

Which companies to target. 

Which roles to apply for.

Which conversations to take.

Which offers to take seriously.

You have the qualities of the companies, people, and roles from your past roles that have led you to success.

You have the qualities of the companies, people, and roles from your past roles that have led you to failure.

You have all the work you’re good at and want to do going forward.

You have your vision of where you want to go.

Combine all of those things into a clear set of characteristics describing the perfect role for you.

The rubric for evaluating any role against your IJD comes down to four criteria:

Does this role give you the skills, experiences, network, and teachers to make your future inevitable, even if the company folds? Does this role have the environment that will allow you to enjoy the work you do and that will set you up for success?

You’ll want to include title and comp, but those are table stakes.

The real question you’re answering is what the role builds you for, not just what it’ll pay you today.

Before you go, make sure to download the playbook:

IMPORTANT NOTE: Your Ideal Job Description is not a static one-time exercise. You will learn things as you network and interview that may lead you to change your target. That’s ok! Our goal is to get started in a direction we’re genuinely excited about and make adjustments from there.

Also, the likelihood you’ll find a role that matches 100% of your IJD is low. The IJD is designed to serve as a rubric for assessing the degree to which the role matches your IJD, not as all or nothing. If it matches most of your IJD, especially the characteristics you’ve marked as your highest priorities, go for it!

If it doesn’t match most of your IJD, you’ll have areas to investigate further or confidence to avoid the role entirely.

Before you go, grab the playbook if you haven't already. It's free, and it's the fastest way to actually do this work rather than just read about it:

[CLICK HERE TO DOWNLOAD THE EARLY COMPLETE CAREER CLARITY PLAYBOOK] (it's free)

Most people spend days updating their resume and LinkedIn and begin applying for anything adjacent to what they’ve done. 

They don’t even spend a few minutes understanding what has led them to be successful in the past, where they are today, and where they want to go.

Three months later, they’re frustrated and confused why they haven’t made any progress.

A true job hunter applies for what they’ve decided they want.

And they can tell the difference between what they want and don’t want because they’ve done this exercise first.

Doing this exercise can be the difference between a 3-month job search that feels enjoyable and a 6+ month job search that’s an absolute grind.

I know which one I’d prefer.

What about you?

Let’s go get you that job! 🏆

Kyle

Founder of Early

P.S. Reply with how you used the playbook, what interview you’re using it for, and what else you wish you had to prepare. I read every reply.